No one loves a good debate quite like baseball fans, and with that in mind, we are following our Top 5 player rankings at each position with the best managers for each franchise, based on their careers while with that club. These rankings are for fun and debate purposes only … if you don’t agree with the order, participate in the Twitter poll to vote for your favorite.
Here is Jordan Bastian's ranking of the top five managers in Cubs history.
1. Frank Chance, 1905-12
Key fact: Highest winning percentage (.664) in team history
One of the great first basemen in club history, he was the final part of the famous Tinker-to-Evers-to-Chance infield trio. And, as a player-manager, Chance oversaw the Cubs during one of the greatest runs in baseball history.
Chance suited up for Chicago from 1898-1912 in what would amount to a Hall of Fame career. He took the managerial reins from Frank Selee in 1905 and then the "Peerless Leader" guided the Cubs to four pennants within five years, winning consecutive World Series in 1907-08. As you may recall, that 1908 title held up as the Cubs' last triumph until the 2016 team ended baseball's longest drought.
With Chance in the manager's chair, the 1906 Chicago club amassed 116 victories, which set a single-season record that held until the 2001 Mariners equaled it. The Cubs averaged 106 wins per season from 1906-10 with Chance at the helm. His 768 wins are the third-most by a manager in Chicago's franchise history.
2. Joe Maddon, 2015-19
Key fact: Franchise-record four consecutive playoff berths
Maddon had earned a reputation as a managerial innovator with Tampa Bay, and the Cubs were aggressive in pursuing him once he became available ahead of the 2015 season. Chicago signed Maddon to a five-year pact to lead a young, emerging Cubs core.
"He changed the franchise forever," Cubs president of baseball operations Theo Epstein said after the 2019 season, when the team did not extend Maddon's contract and instead hired new manager David Ross. "He was the perfect guy for this team at the perfect time. I think everyone who was around the team knows that."
Maddon posted a 471-339 record in five years with the Cubs, leading the team to four playoff berths, including three straight National League Championship Series ('15-17) and a World Series victory in '16. Maddon's .581 winning percentage with Chicago is the second-best in team history among managers with at least three seasons.
3. Charlie Grimm: 1932-38, '44-49, '60
Key fact: Most managerial wins (946) in modern era for Cubs
Just as Maddon reached heights with the Cubs that had not been achieved since the early 1900s, Grimm also led the franchise to some notable moments.
Grimm took over for Rogers Hornsby as manager in 1932, led the team to a 37-18 run down the stretch and captured the NL pennant. He also guided the Cubs to the World Series in '35 and '45. That 1935 campaign included a 21-game winning streak in September and 100 wins overall, marking the most in a season since 1910 (104). It also held as Chicago's last 100-win showing until the 2016 team rattled off 103 victories.
In three stints as Cubs manager, Grimm compiled a 946-782 record (.547 winning percentage). His 14 years at the helm are second in team history only to Cap Anson's 19.
4. Joe McCarthy: 1926-30
Key fact: Earned the first of his nine career managerial pennants with the Cubs
McCarthy is best known as the Yankees' all-time leader in managerial wins (1,460), but his career as a manager began with five years leading the Cubs. He posted a 442-321 record with Chicago, winning the NL pennant during the 98-win 1929 season. McCarthy is perhaps the one that got away for the Cubs, considering he helped New York to seven World Series crowns after being dismissed by the North Siders.
5. Cap Anson: 1879-97
Key fact: Most managerial wins (1,282) in franchise history
Anson served as a player-manager in the early years of the franchise when the club was known as the White Stockings and Colts. After his career was up with the club, it was known as the Orphans for a period, because the team had lost its "Pop" in Anson. While Anson's character issues are well-documented, he is credited with the most managerial wins in team history and helped capture five NL pennants between 1880-86.
Honorable mention
Leo Durocher (1966-72) never won a division title, but he oversaw 535 victories and was at the helm for the beloved '69 Cubs. ... Jim Frey (1984-86) led the '84 Cubs to the NLCS and played a key role in Ryne Sandberg unlocking his power potential. ... Don Zimmer (1988-91) led the '89 Cubs to the NLCS. ... Lou Piniella (2007-10) led the Cubs to back-to-back playoff berths ('07-08) and racked up 316 wins with a .519 winning percentage. ... Dusty Baker (2003-06) won 322 games with the Cubs and a division title in '03. ... Jim Riggleman (1995-99) was in the manager's chair for the '98 season that saw the Cubs win an NL Wild Card berth. ... Frank Selee (1902-05) won 280 games with a .568 winning percentage before the franchise took off under Chance's leadership.